When people talk about the Outlaw Movement in country music, a few names immediately rise to the surface: Waylon Jennings, Willie Nelson, Kris Kristofferson — and often Johnny Cash. All four were later united as The Highwaymen, and all four carried an image of defiance against Nashville’s polished system.
But in a 1998 interview with DJ Johnson of Cosmic Debris, Waylon Jennings made a surprising distinction.
While discussing artists who operated outside the Nashville system, Jennings was asked about himself, Willie Nelson, and Johnny Cash. Waylon didn’t hesitate:
“John’s inside. John’s so inside you wouldn’t believe it. He used to do everything they wanted.”
It wasn’t a personal attack. In fact, Waylon made it clear he loved Johnny Cash and considered him “the biggest — like an Elvis in the business.” But when it came to the music industry structure, Waylon insisted that Cash was never truly an outlaw in the business sense.
To understand Waylon’s point, you have to understand what “outlaw” really meant.
For Jennings and Nelson, rebellion wasn’t just about image. It was about control. In the late 1960s and early 1970s, Nashville record labels tightly controlled studio choices, producers, song selections, and even publishing rights. Artists were often given small royalty percentages, with accounting practices that Jennings later described bluntly as “stealing.”
Waylon fought for artistic freedom — the right to choose his own band, his own producer, and his own sound. He insisted on creative control and ownership at a time when that was almost unheard of in mainstream country. Willie Nelson famously left Nashville and returned to Austin, Texas, helping spark the outlaw movement from outside the system entirely.
In contrast, Jennings suggested that Cash — despite his rebellious persona and black-clad image — continued working within Nashville’s framework.
“He’s never been the rebel,” Waylon said. “Trying to. I don’t think he knows how.”
It’s a provocative statement, especially considering Cash’s larger-than-life image as the “Man in Black,” a champion of prisoners, Native Americans, and the downtrodden. Socially and culturally, Cash was undeniably rebellious. But from Waylon’s perspective, rebellion meant challenging the business structure itself — not just projecting defiance onstage.
Importantly, there was no bitterness in Jennings’ words. He repeatedly emphasized his admiration for Cash. And history shows the respect was mutual. The two would go on to tour and record together as part of The Highwaymen, proving that philosophical differences about Nashville didn’t damage their friendship.
In the end, Waylon’s comments highlight something deeper about the outlaw era: it wasn’t just a sound. It was a fight for autonomy.
Johnny Cash may have worn black and sung for the forgotten.
But according to Waylon Jennings, the real rebellion happened in contract negotiations, studio control, and walking away from a system that tried to dictate the music.
Different kinds of rebels.
Same legendary legacy.